Reaktion #702181

ord-5d555bb2b95b4e60a1015b30955e92d7

Reaktionsgleichung

CCSC1(SCC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
17,17-bis(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4-dien-3-one
→
CCSC1=CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C
tlc-homogeneous material
Ausbeute 87.9%
CCSC1=CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C
17-(Ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4,16-trien-3-one
Ausbeute 87.9%

Edukte

CCSC1(SCC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
17,17-bis(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4-dien-3-one

Reagenzien

Keine

Lösungsmittel

CCc1ccccc1CC
diethylbenzene

Reaktionsbedingungen

Temperatur
190°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe solution is cooled to 0° C.
  2. 2
    Sonstigethe solid that precipitates
  3. 3
    Filtrationis filtered
  4. 4
    workup.DISSOLUTIONThis is redissolved in 1:9 hexane-chloroform
  5. 5
    Sonstigechromatographed on a 60 g-silica gel column
  6. 6
    WaschenElution with 1:9 hexane-chloroform

Vorschrift

A suspension of 1.8 g of 17,17-bis(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4-dien-3-one in 120 ml of diethylbenzene is stirred at 190° C. (oil bath temperature) for 1 hour. The solution is cooled to 0° C. and the solid that precipitates is filtered. This is redissolved in 1:9 hexane-chloroform and chromatographed on a 60 g-silica gel column. Elution with 1:9 hexane-chloroform gives 1.35 g of a tlc-homogeneous material. Crystallization from chloroform-methanol gives 680 mg of the title compound, melting point 282°-283° C., dec.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04146538uspto-grants-1979_03